Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 21:42:57 UTC
Update Date2022-03-07 02:54:57 UTC
HMDB IDHMDB0036559
Secondary Accession Numbers
  • HMDB36559
Metabolite Identification
Common Name(-)-beta-Pinene
Description(-)-beta-Pinene, also known as terbenthene or (1S,5S)-b-pinene, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, (-)-beta-pinene is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on (-)-beta-Pinene.
Structure
Data?1589559485
Synonyms
ValueSource
(-)-NopineneChEBI
(-)-Pin-2(10)-eneChEBI
(1S,5S)-6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptaneChEBI
(1S,5S)-beta-PineneChEBI
(1S,5S)-b-PineneGenerator
(1S,5S)-Β-pineneGenerator
(-)-b-PineneGenerator
(-)-Β-pineneGenerator
beta-PineneMeSH
TerbentheneMeSH
TerebentheneMeSH
(-)-(1S,5S)-beta-PineneHMDB
(-)-2(10)-PineneHMDB
(1S)-(-)-beta-PineneHMDB
(1S,5S)-2(10)-PineneHMDB
(1S,5S)-6,6-Dimethyl-2-methylidenebicyclo[3.1.1]heptaneHMDB
(1S,5S)-Pin-2(10)-eneHMDB
1S,5S-(-)-beta-PineneHMDB
L-b-PineneHMDB
laevo-b-PineneHMDB
2(10)-PinenePhytoBank
6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptanePhytoBank
(±)-2(10)-PinenePhytoBank
(±)-6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptanePhytoBank
(±)-beta-PinenePhytoBank
(±)-β-PinenePhytoBank
NopinenPhytoBank
NopinenePhytoBank
(1S,5S)-(-)-2(10)-PinenePhytoBank
(1S)-6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptanePhytoBank
(-)-(1S)-beta-PinenePhytoBank
(-)-(1S)-β-PinenePhytoBank
(-)-(1S,5S)-β-PinenePhytoBank
(-)-beta-PinenePhytoBank
(1S)-(-)-β-PinenePhytoBank
(1S)-beta-PinenePhytoBank
(1S)-β-PinenePhytoBank
(S)-(-)-beta-PinenePhytoBank
(S)-(-)-β-PinenePhytoBank
(S)-beta-PinenePhytoBank
(S)-β-PinenePhytoBank
l-beta-PinenePhytoBank
l-β-PinenePhytoBank
Chemical FormulaC10H16
Average Molecular Weight136.234
Monoisotopic Molecular Weight136.125200512
IUPAC Name(1S,5S)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptane
Traditional Name(-)-β-pinene
CAS Registry Number18172-67-3
SMILES
CC1(C)[C@@H]2C[C@H]1C(=C)CC2
InChI Identifier
InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3/t8-,9-/m0/s1
InChI KeyWTARULDDTDQWMU-IUCAKERBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Pinane monoterpenoid
  • Bicyclic monoterpenoid
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-61 °CNot Available
Boiling Point165.00 to 167.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility7.06 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.239 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.064 g/LALOGPS
logP3.94ALOGPS
logP2.86ChemAxon
logS-3.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.65 m³·mol⁻¹ChemAxon
Polarizability17.14 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.35131661259
DarkChem[M-H]-131.27531661259
DeepCCS[M+H]+136.21330932474
DeepCCS[M-H]-133.81730932474
DeepCCS[M-2H]-168.16930932474
DeepCCS[M+Na]+142.72330932474
AllCCS[M+H]+128.032859911
AllCCS[M+H-H2O]+123.532859911
AllCCS[M+NH4]+132.232859911
AllCCS[M+Na]+133.532859911
AllCCS[M-H]-132.432859911
AllCCS[M+Na-2H]-133.932859911
AllCCS[M+HCOO]-135.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(-)-beta-PineneCC1(C)[C@@H]2C[C@H]1C(=C)CC21100.3Standard polar33892256
(-)-beta-PineneCC1(C)[C@@H]2C[C@H]1C(=C)CC2978.5Standard non polar33892256
(-)-beta-PineneCC1(C)[C@@H]2C[C@H]1C(=C)CC2966.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - (-)-beta-Pinene EI-B (Non-derivatized)splash10-002f-9000000000-30fa40ae82c24567182c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (-)-beta-Pinene EI-B (Non-derivatized)splash10-002f-9000000000-30fa40ae82c24567182c2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-beta-Pinene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-1900000000-7a8b637e362b2868237d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-beta-Pinene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-beta-Pinene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-beta-Pinene 10V, Positive-QTOFsplash10-000i-0900000000-e26a5aa072ee3c657bb12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-beta-Pinene 20V, Positive-QTOFsplash10-000i-0900000000-9ce03af98198cbec9a562016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-beta-Pinene 40V, Positive-QTOFsplash10-00dr-0900000000-83547c837f75972195a62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-beta-Pinene 10V, Negative-QTOFsplash10-000i-0900000000-ae6e9f2df0d7b06fe3be2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-beta-Pinene 20V, Negative-QTOFsplash10-000i-0900000000-5e150dd4370565464dad2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-beta-Pinene 40V, Negative-QTOFsplash10-014r-0900000000-45b2edf143e15a1e58672016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-beta-Pinene 10V, Negative-QTOFsplash10-000i-0900000000-a013b4ae27f975ab56212021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-beta-Pinene 20V, Negative-QTOFsplash10-000i-0900000000-a013b4ae27f975ab56212021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-beta-Pinene 40V, Negative-QTOFsplash10-000i-0900000000-7260f27ae84d64a57ad42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-beta-Pinene 10V, Positive-QTOFsplash10-000i-0900000000-32bfa268614bcd6c4f812021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-beta-Pinene 20V, Positive-QTOFsplash10-000i-0900000000-32bfa268614bcd6c4f812021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-beta-Pinene 40V, Positive-QTOFsplash10-059i-0900000000-b224f82915803ce924fc2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015463
KNApSAcK IDC00000806
Chemspider ID389794
KEGG Compound IDC06307
BioCyc IDCPD-4891
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440967
PDB IDNot Available
ChEBI ID28359
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1108611
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ishida T, Asakawa Y, Takemoto T, Aratani T: Terpenoids biotransformation in mammals III: Biotransformation of alpha-pinene, beta-pinene, pinane, 3-carene, carane, myrcene, and p-cymene in rabbits. J Pharm Sci. 1981 Apr;70(4):406-15. [PubMed:7229954 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.